Cow Key Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cow Key vacation rentals

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
$959 nightly
The price is $1,079
May 13 - May 14
Total with taxes and fees
Atlantic View Luxury Villa with Pool

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
$518 nightly
The price is $583
May 13 - May 14
Total with taxes and fees
Ocean Front One Bedroom Residence

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
$1,099 nightly
The price is $1,229
May 10 - May 11
Total with taxes and fees
Lighthouse Suites Collection

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
$1,160 nightly
The price is $1,305
May 13 - May 14
Total with taxes and fees
Contra House Key West

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (183 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
$291 nightly
The price is $327
May 17 - May 18
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (6 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
$501 nightly
The price is $563
May 18 - May 19
Total with taxes and fees
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
$788 nightly
The price is $886
May 14 - May 15
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views

The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
$2,171 nightly
The price is $2,442
May 17 - May 18
Total with taxes and fees
The Fairhaven House at Solaire Lunara Bay

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
$1,882 nightly
The price is $2,118
May 19 - May 20
Total with taxes and fees
Waterfront Luxury Home - Tidelands House

Palmgale House in Key West

Palmgale House in Key West
2.0 star property
Raccoon Key
$1,590 nightly
The price is $1,789
May 12 - May 13
Total with taxes and fees
Palmgale House in Key West

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
$584 nightly
The price is $657
May 10 - May 11
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront

Floralee House in Key West

Floralee House in Key West
2.0 star property
Raccoon Key
$2,112 nightly
The price is $2,376
May 10 - May 11
Total with taxes and fees
Floralee House in Key West

Aquaria House by Brightwild Pool Boat Dock

Aquaria House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
$1,317 nightly
The price is $1,481
May 12 - May 13
Total with taxes and fees
Aquaria House by Brightwild Pool Boat Dock

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
$1,353 nightly
The price is $1,522
May 19 - May 20
Total with taxes and fees
Capmar House by Brightwild Huge Home Pool

Brand New The Greenmoor House With Pool

Brand New The Greenmoor House With Pool
2.0 star property
Raccoon Key
$1,649 nightly
The price is $1,855
May 12 - May 13
Total with taxes and fees
Brand New The Greenmoor House With Pool

Springtide House by Brightwild Waterfront Pool

Springtide House by Brightwild Waterfront Pool
2.0 star property
Raccoon Key
$1,317 nightly
The price is $1,481
May 12 - May 13
Total with taxes and fees
Springtide House by Brightwild Waterfront Pool

Parking Pool Dock - Shellstone House

Parking Pool Dock - Shellstone House
2.0 star property
Raccoon Key
$1,852 nightly
The price is $2,084
May 21 - May 22
Total with taxes and fees
Parking Pool Dock - Shellstone House

New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
2.0 star property
Raccoon Key
$1,885 nightly
The price is $2,121
May 12 - May 13
Total with taxes and fees
New Waterfront Home - Dreamside House

The Joyrise House at Solaire Lunara Bay

The Joyrise House at Solaire Lunara Bay
2.0 star property
Raccoon Key
$1,853 nightly
The price is $2,085
May 12 - May 13
Total with taxes and fees
The Joyrise House at Solaire Lunara Bay

Waterlane House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
$1,415 nightly
The price is $1,592
May 12 - May 13
Total with taxes and fees
Waterlane House by Brightwild Pool Boat Dock
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Cow Key Hotel Reviews

Find out more about Cow Key

Everything you need to know about Cow Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cow Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cow Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cow Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cow Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cow Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $319 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cow Key rentals

At Expedia, we put the best Cow Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cow Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cow Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cow Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Cow Key?

Yes, we have vacation rentals near well known local attractions in Cow Key, or you can select a more secluded option if you're looking for relaxation. Cow Key is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

What are some of the best vacation rentals that Cow Key has to offer?

Sugarloaf Key RV Resort & Cottages: Visitors like this Cow Key vacation home rental. It is located near a metro station and offers an outdoor pool, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

What can I see and do in Cow Key?

Explore the area and family-friendly sights such as Mel Fisher Maritime Museum, or get out into nature at a spot like Florida Keys Beaches. In the larger area, you’ll find Duval Street and Key West Tropical Forest and Botanical Garden.

What are vacation rentals like in Cow Key?

Vacation rentals are private accommodations you can stay in for several days or more in Cow Key. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.